


Diana and Joey

by InfinityOnDrugs



Category: Original Work
Genre: Adultery, Age Difference, Babysitting, Blow Jobs, Cheating, Creampie, Dom/sub Undertones, Dominance, F/M, Femdom, First Time Blow Jobs, Fucking, Hand Jobs, Light Dom/sub, Loss of Virginity, Making Love, Making Out, Manipulation, Rough Sex, Roughness, Shotacon, Teaching, Underage - Freeform, Underage Sex, Virginity
Language: English
Status: Completed
Published: 2020-05-07
Updated: 2020-05-07
Packaged: 2021-03-03 04:33:36
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,651
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24059032
Author URL: https://archiveofourown.org/users/InfinityOnDrugs/pseuds/InfinityOnDrugs
Summary: On his 18th birthday, Jessie's girlfriend Diana gets him tickets to see a basketball game, offering to stay at home and watch his eleven year old brother Joey. Little does Joey know Diana has their whole night planned out ahead of them, and it isn't going to be spent playing rounds of Monopoly.
Comments: 8
Kudos: 90





	Diana and Joey

“I’m sorry Jessie, I really wish there was something I could do.” Diana draped her arms across Jessie’s shoulders consolingly.

“Aah, forget about it. This ain’t the first time they’ve been called out for an emergency business meeting. But I just don’t understand how an emergency in a business such as paper-making arises so quickly!”

“I’m sure it’ll all work out Jessie, I’m sure it’ll _all_ work out.”

“I dunno. I’m stuck here now babysitting Joey, so I’m tied until they get back.” Jessie’s eleven year old brother silently hummed to himself as he played with a toy truck in the other room. There was no way he’d be able to get out of the house and leave him on his own, not even for an hour.

“I wouldn’t be so sure.” Diana whispered into Jessie’s ear.

Jessie turned to face Diana, “Wouldn’t be so sure? Good god Diana, now what could you be suggesting?”

Although a few months ago she’d of loved to dig into the blond in front of her for some carnal pleasures, she had other thoughts in mind for the night.

“Well, I’d be a shitty girlfriend if I didn’t get my boo a nice birthday present, right?”

“Maybe you’re right,” Jessie said with a smile, sliding his fingers across Diana’s waist, “now that you’re here, maybe this birthday won’t be to bad after all.”

“Uh uh uh.” Diana said, wagging a finger onto Jessie’s lips, “Are you sure you want _this_ measly gift?”

“Measly?” Diana was a tall noirette, with copious amounts of straight black hair. Measly couldn’t describe a single aspect of her; not her smooth olive skin, not her perky 34F cups, not her long legs accented by her flowing black skirt, and certainly not her supple, 90 degree ass. “...Measly? Please baby, you’re nothing like a meas.”

Even though Jessie was almost a sexaholic, Diana knew he had one paralyzing weakness above all else. She smiled a wicked smile, “Well, it’s relative. You do know the Hornets are playing the 76ers tonight, right?”

Jessie pulled back, eyes widening with surprise, “You don’t mean...”

“Yes I mean!” Diana pulled an envelope from her back pocket, and Jessie looked inside.

“Three tickets! How’d you get these!?”

“raffle at my job, and with some pitying pouts, I figured I could surprise my boyfriend with a bit of a present.”

“So it’s one for me, you, and… Joey?”

Diana giggled as a car honked out front, “No silly! For you and your friends! Forget about the hassle and stress about babysitting your brother, I do babysitting on the side anyways. I just want you to have the best birthday you could have.”

Jessie gave Diana a huge hug, “You sure you can handle Joey? You really don’t have to do this.”

“Of course I do! What kind of girlfriend would I be if I didn’t?” The car honked again outside, “I called Noah to pick you up, so your chariot awaits.”

As fast as a giddy kid at Christmas Jessie grabbed his coat and swung out the door, “I owe you for this, I’ll pay you back!”

Diana watched as he shut the door and ran out to the car, “Oh baby, you’re already paying me plenty.”

  


* * *

  


Diana did not like Monopoly. Joey on the other hand loved loved it. Especially when he was rolling doubles every other turn; this turn, it was a solid 12. They’d been playing for the past hour, and her criss-crossed legs were falling asleep. Still, she followed her plan.

“Wow Joey, you’re really good at this!”

“Thank you Ms. Diana!” he said beaming with pride. He looked like a spitting image of Jessie when he was eleven, the same falling hair, the same crazy grin. When Diana first start going out with Jessie, she though she was just seeing pictures from when Jessie was younger. But when she found out that he had a brother, all her focus started to shift.

“Hey Joey, I know that monopoly is really fun, but after this do you want to play a really fun adult’s game?”

“But this is an adult’s game.”

“Well duh! But the game I’m thinking of is, well, I don’t know, reserved more for older kids, I probably shouldn’t have even brought it up.”

Joey didn’t take the bait. He really, _really_ loved monopoly.

“But… what about monopoly?”

“How about this Joey,” Diana quickly glanced around the board, “if you win, you can choose the next game that we play, and it can be monopoly if you want. But if I win, we get to play my game.”

“Deal! But we’re going to play Smash bros.!”

Joey looked back to the board to move his racecar. He probably should have moved his piece before making the deal; he was on his own safe Ventnor Avenue, but now veering onto Diana’s dangerous stretch of hoteled greens and blues. He looked puzzled for a second, and then realized what had happened.

“Hey!”

“Deal’s a deal Joey, I’m sorry.”

Joey crossed his arms with a sour look on his face, “You knew I was going to lose, didn’t you.”

“Oh don’t be so down, Joey, I just know you’ll win at our next fun activity.” 

“But I don’t want to play!”

Diana seductively leaned across the board on all fours, her loose shirt airing out, hanging in the air with her bra and tits, as she stared down Joey right in his face, “Are you sure?”

Joey looked at Diana silently and gulped, “I dunno, I think I can give it a try.”

“Perfect!” Diana started to unbutton her white blouse, exposing her lacy black bra, “Come on, take off your shirt.”

“What?” 

“It’s how you play the game, silly! Here, I’ll help.” Diana stood up, finally getting blood back to her legs, and walked around to Joey. She giggled, noticing that Joey was staring transfixed at her bosom. _This may be easier than I expected_ , she thought, kneeling back down behind Joey.

“Lift your arms.” Joey did as he was told, awkwardly holding his hands in the air as Diana grabbed the bottom of his shirt and pulled up. The only time in recent memory his shirt was off with someone else was when he was at the doctors for his checkup. He remembered the weird, vulnerable feeling, and felt himself blush as it began to resurface. Diana noticed and giggled again.

“Don’t worry Joey, this game doesn’t hurt at all. In fact, you’ll find it quite enjoyable.”

Joey began to breath heavily as Diana’s hand started drifting down to his pants, “But, Ms. Diana, this feels kind of funny...”

“Do you trust me Joey?” Diana whispered into his ear.

Joey turned his head to look at Diana. Her warm, inviting smile, her piercing green eyes; she had always been really nice to him. Always smiling and playing with him when she’d come over, she’d even gotten him one of those mini-lego kits he had wanted for his birthday. With her he always felt safe, like nothing bad could ever happen. She’d be there to protect him, to gently help him. Joey drew a shaky breath as Diana’s hand dipped into his cargo shorts, “Yeah.”

“Good.”

Diana hugged her arm around Joey’s chest, pulling him back into her. Her other hand grabbed onto his cock through his underwear, messaging it around. Joey’s breath spiked as his face went completely flush. No one had ever touched him down there, not even himself, and especially not like this. He closed his eyes and clenched his teeth as his lower body was met with a rush of uncomfortable new feelings.

Diana could feel Joey’s heart racing in his little chest. Her own heart started racing, adrenaline pumping as she fully realized what she was doing. Months of waiting had led up to this point, planing and plotting with Joey. But it was all worth it, to finally get with the cute little boy she had been pining for ever since she laid eyes on him. Jessie be damned.

Joey’s blood began flowing into his penis as his erection grew in his pants. Diana guessed from her fingers he must have been 5, 5.5 inches long, and still growing. His precum started to wet his underwear at the tip of his cock, so Diana pulled her hand out and unbuttoned his shorts, pulling them and his underwear down. His 6 inch cock stood full salute twitching and throbbing; puberty must have hit a bit early for the little boy. Diana’s hand went back to jacking his cock, slowly and methodically climbing and dropping. Her thumb was kept on his tip, swirling and playing with his most sensitive part. Joey felt it right away, letting out a small weak mewl as he tried to squirm in Diana’s clutch. But she held him firmly to her chest, his head resting in between her boobs.

“See what happened with your penis Joey?” She whispered warmly into his ear, “This is called an ‘erection’, and what I’m doing is called a ‘handjob’. Does this feel good Joey?”

Joey felt like his cock was getting tickled through and through. He felt a pressure, rising from deep inside his guts, like a hot touch cradling him. His frame shivered from the gentle touch of Diana’s deft hands playing with his cock, “This fe-els… weird.”

“Well, I promise Joey, it’ll feel real good real soon.”

Joey’s breath began to quicken, his chest rising and lowering faster and faster; He was close to his very first orgasm. But right before he finally came, Diana stopped, letting go of his cock and pulling her hand off. She didn’t want to be cruel, to rob Joey of the short term pleasure, but they still had the whole night together and she wasn’t about to end their game now. Joey began to catch his breath, his cock still stood at full mast, twitching and leaking precum.

“You’re very good at this Joey.”

“Ms. Diana? I-I still feel funny.”

“I know baby, it’s because we’re not done playing the game. Do you have a bedroom?”

Joey nodded his head.

“Well, the next part is much more fun if we play it there. Can you show me it?”

  


* * *

  


“And this is my bed.” Joey said, gesturing to his bed.

“Wow, that’s a big boy bed!” Joey blushed again, “I think it’s just perfect to finish our little game, don’t you think?”

“Well, I guess. So, uh, what next?”

“I think you’re ready to move onto the next level. Get on the edge of the bed.” Diana turned Joey to face her and sat him right on the edge. After propping her phone on the dresser, she knelt down in front of Joey and began to undo his belt again, licking her lips as she worked. The bulge in his underwear was still wet and semi-hard, so after his shorts and undies fell it took only a few seconds to once more get fully erect. Apparently a part of Joey really was enjoying this new game.

“This is what’s called a ‘blowjob’, or ‘fellatio’.” Diana tossed his shorts and underwear to the side next to his hamper leaving him sitting legs dangling off the edge of the bed completely naked. Joey never had a girl in his room before, and when he figured he finally would he certainly never thought it would be like this. He figured they’d play a video game, like Smash bros., or Monopoly (which he really liked), but not a game like this. Not that he was complaining. Although it was a new experience, and he was feeling really awkward and funny around his penis, it was a good kind of funny. And besides, he was playing with Diana. The first part of the game had been fun and warm being wrapped in her embrace, so the next level must be fun.

Diana’s lips connected with the tip of Joey’s cock, taking the first inch onto her tongue. The kid let out a sharp gasp; a handjob was one thing, but feeling the wet teasing movements of her mouth on his tip was a whole different experience. His face twisted back to that embarrassed little kid look he had during the handjob as he leaned back onto his elbows. Diana pulled her lips back slowly to the tip, but right before she kissed the tip off, her head fell back down an inch. She kept repeating this, savoring the taste of the young boys manhood, trying to prepare him for the next level after this.

After a few slurps from Diana and some _oh_ ’s and _ah_ ’s from Joey, Diana began to push her head a little bit deeper into him. Expertly she sucked on his member, keeping a tight ring with her lips and teasing the whole length in her mouth with her tongue. Sure she was experienced – sometimes Jessie was horny after a date and she didn’t want to have to go through the motions of a fucking – but for Joey she was giving it everything she had. After all, she could at least give him a great and pleasurable experience if she was going to be the one to take his virginity.

She made sure to maintain full eye contact upwards toward Joey as she went. When Joey looked down at Diana, he turned his head to the side looking away, clearly embarrassed. He couldn’t shake the uncomfortable feeling growing inside him, even if it did feel strangely good.

“Don’t be shy Joey, you’re doing great!” Diana pulled her mouth off his cock and kept it in motion with her hand, “It’s much more fun to look. Come on, watch me suck your cock.”

Joey sheepishly turned back to Diana and stared back into her piercing green eyes. She giggled again and turned her head down while keeping contact, fluttering her eyelashes and giving him her best doe eyes. Joey laughed himself at her funny expression through his coos of pleasure.

As Diana worked her lips up and down his member she shrugged her blouse off her shoulders, shaking and taking it off, tossing it by Joey’s clothes. She kept rhythm and pace as she reached behind herself to unclasp her bra. A drop of slimy spit dribbled down her chin as she pulled the straps off round front and tossed it to her blouse. Grabbing onto the base of Joey’s cock, Diana started going faster and faster. 

Once again, Joey felt a rising sensation from his lower body, like a muscle tense all over he couldn’t – or wouldn’t want to – control; a quake of pleasure, pulsing and throbbing down below. But just like with the handjob, Diana had to stop herself. The next level was the real deal, and she wanted him all worked up for it.

Diana pulled her mouth off of Joey’s cock with a suction cup _plop_ , and for a second after it twitched as if it was still going to burst with it’s load. But after two wags, it remained silent. Joey looked like he had tried to sneeze, but before he was able to it had gone. His body had been anticipating some release; his adrenaline was pumping like crazy and he was flush with awkward excitement, but he was cut off right before his reproductive climax.

“Um, Ms. Diana?” Joey managed through his panting.

“Hm?” Diana had wiped the drooling spit off her upper chest and chin and started to take off her skirt.

“I-I still, even after that – i-it was fun, I really liked it – but I, feel, like… funny, still.”

“Of course you do, because we’re not done yet,” Diana said, tossing her skirt off to the side as she hooked onto her panties, “There’s one final level!”

Diana dropped her panties, revealing her shaved pussy. It was still very tight – she had tried to keep Jessie at blowjob and handjob level, only doing penetrative sex when she really needed a fix. He was just too touchy and pushy and gropey in bed when she tried to ride him, or worse, when he clumsily tried to top her. It just wasn’t as enjoyable as it could be for Diana, hence why Joey was such an appealing target.

“Now Joey, normally, this part is called ‘sex’,” She swung Joey’s legs onto the bed and crawled over top him. In the shadow of her much larger frame, he looked like a sad puppy, scared and defenseless, ripe for her taking, “But what we’re going to do is called ‘fucking’, which is much, much more fun. Ready?”

It was a rhetorical question. She made him ready. 

Diana straddled herself across Joey’s stomach on her knees. She guided his 6 inches as she began to sit back, making sure they hit their hit their mark and slid in nice and easy. The tip pushed into Diana’s aching wet pussy, and inch by inch she lowered herself down to the hilt. His cock hit right where she needed it to, and she shuddered with the pleasure of it reaching her G-spot. Joey mewled and started breathing heavily from his cock getting coated and warmed and squeezed more pleasurably than before. Diana leaned forward, putting her hands onto Joey’s arms, further pinning him into his bed. Joey let out a shout of surprise; he didn’t expect the game to get so rough and physical. But Diana was making true to her word: she didn’t intend to ride Joey, she intended to fuck.

Diana began to move her hips slowly back and forth. She wanted to keep pacing herself with Joey, to let the poor kids experience last a good length of time before ending. He was almost off the edging high from the blowjob, but she didn’t want to take the chance. His cock twitched inside of her, he could feel it getting pulled up and pushed down in perfect time with her swaying hips. It was impossible to squirm, to try to push his cock deeper into her, even though he felt the sudden distinct urge to do so. Diana was stronger than most girls her age thanks to a healthy workout schedule, and there was no possible way that an eleven year old could overpower a seventeen year old. So Joey laid back, his breath coming faster, the feeling in his legs growing weak as the feeling of his cock getting stimulated become more and more prominent. Joey still felt the weird pressure in his guts, but now, he was feeling happier about it. It felt like he had just run the length of the recess field, the exhilarating happiness from a physical workout overpowering any pain or negativity. 

After establishing a rhythm, Diana began to pick up her pace with her hips. Slowly like a crescendo she started moving less and humping more, pushing Joey’s hips deeper and deeper into the mattress. It was hard having to hold herself back from tearing into the little boy, her mind obsessed with the salty taste of his cock, the feel of it throbbing and growing in her hands. All she wanted now was to truly make love with the confused, childish mate she had beneath her, to fuck and push and coddle and be with him. She felt his cock start poking back into her special zone, and Diana began pushing directly onto that spot.

A crazed look of pleasure crossed Diana’s face as she felt her inside’s twitch around the little kids cock, her G-spot getting slammed each hip thrust by its tip. Joey didn’t know whether to be afraid of what emotions she was feeling, to try to convulse and twitch free of her iron grip and hump himself, ornot even think at all and drift through the intense physical ecstasy pounding through his small body.

He winced as he felt her huge hips and thighs slap into his own. He was completely stuck, there was nowhere he could squirm or crawl out to; she held him entirely in place. Not like he wanted to stop, or even could. The pleasure he felt in the handjob, the wet wamrth he felt from her blowjob, it was all combined and magnified into the slamming and humping of her vagina around his cock.

Diana looked down at Joey, breathing heavily from the workout she was straining from her hips. He was panting just as heavily as she, maybe even more so. Through his squinting eyes Diana saw him stare at her boobs, transfixed as they flew up and down in time with Diana’s humps.

“Here baby,” Diana held up a tit to Joey’s face, “I know you’ve been eying these. Go on. Suck em’.”

Joey stared back at her with an innocent and puzzled face, unsure about what she wanted him to do. Diana sighed and paused her humping for a second, letting her hands off his shoulders.

“Like this, see?” She took her left boob and put the nipple in her own mouth. Sucking on it drew her own pleasure, but it didn’t compare to having someone else play with them. Joey got the idea and cautiously grasped her other boob with both his hands, putting his mouth on the nipple. Slowly he mimicked her own motions, sucking and tugging on her nipple, teasing it with his tongue. Diana blushed with pleasure, surprised at this little boys sudden skill; not even Jessie was as good at handling her boobs as his younger brother was. “That’s it Joey, that’s it.”

She began humping into his cock again with ferocious energy. Certainly she wasn’t lactating and Joey wasn’t getting rewarded with a stream of fresh breast milk, but that childish instinct of sucking off a mother’s tit kicked in, and Joey went full on with her boob. It was the only thing he could think of as his mind swirled from his cock getting fucked by Diana’s tight pussy. 

Eventually Diana got back into a wild rhythm as she ground herself deep into Joey’s crotch, having to support herself with an arm into the bed so as to let Joey keep suckling. For once it felt good to be in control of fucking, to not have to deal with incessant groping and instead be focused on creating pleasure, both for herself and her lucky Joey. She looked down at the boy, completely shrouded by her shadow, kneading and playing with her boob. He gazed back so innocent and so pure, completely open to whatever Diana wanted from him. There was not want or need from him like Jessie, she didn’t have to bend over backward and go out of her way to please him. He just did what she wanted him to do.

Diana leaned into him, pulling her tit out of his mouth. He looked surprised for a second before she kissed him full on the lips. Joey let out a stifled mewl, completely unheard as he was smothered by Diana’s passion and the sound of wet slapping. Diana kept at him, opening his mouth with her tongue.

“Tha-at,” Diana whispered between pants, her mouth only an inch away from his, “is ca-alle-ed ‘Ki-issi-ing’.”

Diana swirled her tongue around Joey’s mouth as her hands encircled his head, grabbing and combing through his tufts of hair. She kept grinding into Joey, milking his cock up and down left and right forwards and backwards. Her body completely covered his, her breasts pulsated against his heartbeat, her legs twisted and intertwined with his legs, her tongue slid over his tongue. It wasn’t long before the heavenly feeling of her womanhood became too much for the little boy, and for the third time that night, he felt his body start to tense as a familiar pressure vibrated through his entire body.

Diana knew he was going to blow soon, so she dug deeper into him. Her whole body rubbed against Joey’s as she clawed and scratched him, biting into his lower lip. He didn’t mind, he loved the feeling. Her hips rocked vigorously over his cock, swinging wildly back and forth, coaxing more and more pressure in his cock, drawing his orgasm to it’s wild, carnal climax.

Diana felt a hot liquid shoot into her insides as Joey bucked his hips. Diana had him completely pinned beneath her onto the bed, so it was less of a bucking motion and more of a harsh convulsion. He pushed twice more, accompanied by similar spurts of spunk into her womb, and Diana climaxed as well, her head flying back as she let out a high pitch shout of animalistic pleasure. As his muscles let go of their tension, Joey relaxed back into the bed, exhausted and spent from the frenzied fucking he’d just received, his body shuddering from the hot sweat pouring out of him. Diana rolled off of him and laid next to him, catching her own erratic and labored breath as the boy’s fresh creampie oozed out of her. 

She wasn’t worried about the kid shooting off inside, she had been sure to take the pill for the past while in anticipation. But even so, it was a weird feeling even for her. Diana had made sure to never let Jessie cum inside of her. She disliked the sensation and the messy cleanup that always came after. But with Joey, she felt like it was the least she could do to repay the boy for his troubles. And he was still only eleven years old, so his sperm would have very little chance to actually impregnate her anyway.

They laid there still, letting the bedroom air cool their burning bodies, allowing their lungs to draw in heavy breaths, regaining all their expended strength and energy. The weird and uncomfortable pressure Joey felt stuck inside of him was now released and replaced with a warm, dizzying ecstatic haze. He drooled a little as he smiled, waves of pleasure still flowing from his cock. Diana’s game was much more fun than a childish game of Monopoly, he was sure of that.

  


* * *

  


A few minutes passed before Diana regained her strength and her orgasmic pleasure subsided.

“Hey Joey,” She propped herself up by her elbows to look down at her new lover with ever more enthusiasm. Her hair was frizzled and black strands covered part of her vision, but she didn’t mind, “Wasn’t that fun?”

Joey smiled and tiredly nodded his head, still nakedly panting from the rough fucking he just got.

“Now, don’t tell your brother about this, okay?”

“Why?”

“Well, you beat your brothers highscore! You wouldn’t want to make your brother feel bad, would you?”

“I… I guess not.”

“You’re a good little brother Joey,” She kissed him on his cheek, “now I think it’s just about your bedtime.”

“Awww...”

Diana pushed her self up and over the edge of the bed, getting a rush of blood to her still dizzy head. Her hips and legs were sore and worn down, but she had to clean up before Jessie got back. She grabbed her phone off the dresser and picked up her blouse, skirt, panties et al. Before she left, she tucked Joey under the covers, giving him another gentle kiss on his forehead.

“Um, Ms. Diana?”

“Yeah?”

Joey played with his sheets, “Can we play this again sometime?”

Diana smiled, her plan working better than she could have ever hoped, “Of course we can Joey. Next time I’m over, we’ll play this all night long.”

They said goodnight and Diana turned off his light as she left the room. She’d take a shower, wash off the kid spunk in her pussy, and still have another hour before Jessie was due home. _Plenty of time to enjoy this_ , she smirked to herself, pressing play on her phone as she closed the bathroom door.

_“This is what’s called a ‘blowjob’, or ‘fellatio’.”_


End file.
